HCID 68487848, compound → HCID 59167758, compound

HRID 1616571Notes

Reaction equation

HRID 1616571 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([C:8]2[CH:12]3[CH2:13][CH2:14][CH2:15][O:16][CH:11]3[O:10][N:9]=2)[CH:7]=1>Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([C:8]2[C:12]([CH2:13][CH2:14][CH2:15][OH:16])=[CH:11][O:10][N:9]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 68487848HCID 68487848, compound

Product 1

HCID 59167758HCID 59167758, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Heat a solution of 3-(5-chloro-2-methoxyphenyl)-3a,5,6,7a-tetrahydro-4H-pyrano[3,2-d]isoxazole (12.0 g, 44 mmol) in 12 N HCl (200 mL) at 50° C. for 24 hours and then dilute the mixture with water (300 mL) and extract with ethyl acetate (3×200 mL). Wash the combined organic extracts with brine (100 mL), dry over Na2SO4 and remove the solvents under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate/hexanes (1:1), to provide 3-[3-(5-chloro-2-methoxyphenyl)isoxazol-4-yl]propan-1-ol (8.0 g, 68%).

Workup

  1. extractionextract with ethyl acetate (3×200 mL)
  2. washWash the combined organic extracts with brine (100 mL)
  3. dry with materialdry over Na2SO4
  4. customremove the solvents under reduced pressure
  5. customPurify the residue by flash column chromatography on silica gel
  6. washeluting with ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-0338672e8c63488580dfe067b88eae6b
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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